Conditions | Yield |
---|---|
With P(MeNCH2CH2)3N In hexane; acetonitrile at 25℃; for 0.5h; | 92% |
With silver(l) oxide | |
With ethanol; magnesium ethylate |
Conditions | Yield |
---|---|
With potassium carbonate; N-benzyl-N,N,N-triethylammonium chloride In N,N-dimethyl-formamide at 60℃; for 4h; | 90% |
With potassium carbonate; N-benzyl-N,N,N-triethylammonium chloride In N,N-dimethyl-formamide at 60℃; for 4h; Product distribution; other solvent, other temperature, other reaction time; | 90% |
With sodium acetylide In benzene at 20 - 25℃; for 0.5h; further reagent (sodium phenylacetylide); | 89% |
Conditions | Yield |
---|---|
With samarium diiodide; tris(dibenzoylmethano)iron(III); tert-butyl alcohol In tetrahydrofuran for 0.5h; Ambient temperature; | 89% |
With hydrogen; palladium on activated charcoal In methanol Product distribution; | |
With (5,10,15,20-tetrakis-4-tolylporphyrinato)(methyl)rhodium(III); isopropyl alcohol In benzene-d6 at 200℃; for 48h; Darkness; Sealed tube; regioselective reaction; | 14 %Spectr. |
diethyl ethylidenemalonate
BuMnCl
A
diethyl (1-methyl-pentyl)malonate
B
ethyl diethyl malonate
Conditions | Yield |
---|---|
In tetrahydrofuran at -30℃; for 2h; | A 87% B 6% |
diethyl ethylidenemalonate
butyl-iodo-manganese
A
diethyl (1-methyl-pentyl)malonate
B
ethyl diethyl malonate
Conditions | Yield |
---|---|
In diethyl ether at -30℃; for 2h; | A 83% B 11% |
diethyl ethylidenemalonate
A
diethyl (1-methyl-pentyl)malonate
B
ethyl diethyl malonate
Conditions | Yield |
---|---|
In tetrahydrofuran at -30℃; for 2h; | A 82% B 12% |
diethyl ethylidenemalonate
A
diethyl (1-methyl-pentyl)malonate
B
ethyl diethyl malonate
Conditions | Yield |
---|---|
In tetrahydrofuran at -30℃; for 2h; | A 82% B 8% |
diethyl ethylidenemalonate
A
diethyl (1-methyl-pentyl)malonate
B
ethyl diethyl malonate
Conditions | Yield |
---|---|
In tetrahydrofuran at -30℃; for 2h; | A 80% B 7% |
n-butyllithium
diethyl ethylidenemalonate
methylaluminum dichloride
A
diethyl isopropylmalonate
B
diethyl (1-methyl-pentyl)malonate
C
ethyl diethyl malonate
Conditions | Yield |
---|---|
Stage #1: n-butyllithium; methylaluminum dichloride In hexane; toluene at -40℃; for 1h; Substitution; Stage #2: With boron trifluoride diethyl etherate In hexane; toluene for 1h; Addition; Stage #3: diethyl ethylidenemalonate In hexane; toluene at -40℃; for 18h; Reduction; Michael addition; | A 7 % Chromat. B 74% C 6 % Chromat. |
diethyl ethylidenemalonate
C3H7ClMn
A
diethyl 2-(3-methylbutan-2-yl)malonate
B
ethyl diethyl malonate
Conditions | Yield |
---|---|
In tetrahydrofuran at -30℃; for 2h; | A 70% B 11% |
bronidox
A
5-(1,3-dioxa-5-cyclohexylidene)-1,3-dioxane
B
5-nitro-5-(5-nitro-1,3-dioxa-5-cyclohexyl)-1,3-dioxacyclohexane
C
ethyl diethyl malonate
Conditions | Yield |
---|---|
In dimethyl sulfoxide at 20℃; for 12h; Yield given; | A n/a B 11% C n/a D 67% |
In dimethyl sulfoxide at 20℃; for 12h; | A n/a B 11% C n/a D 67% |
diethyl ethylidenemalonate
tert.-butyl lithium
methylaluminum dichloride
A
diethyl isopropylmalonate
B
diethyl 2-(3,3-dimethylbutan-2-yl)malonate
C
ethyl diethyl malonate
Conditions | Yield |
---|---|
Stage #1: tert.-butyl lithium; methylaluminum dichloride In hexane; toluene; pentane at -40℃; for 1h; Substitution; Stage #2: With boron trifluoride diethyl etherate In hexane; toluene; pentane for 1h; Addition; Stage #3: diethyl ethylidenemalonate In hexane; toluene; pentane at -40℃; Reduction; Michael addition; | A 2 % Chromat. B 66% C 6 % Chromat. |
Conditions | Yield |
---|---|
Stage #1: hex-3-yne With diisobutylaluminium hydride In n-heptane; toluene at 50℃; for 3h; Addition; Stage #2: diethyl ethylidenemalonate In n-heptane; toluene at -40℃; for 18h; Michael addition; | A 21 % Chromat. B 43% |
4-O,O-t-butyl 1-ethyl 2-(ethoxycarbonyl)monoperoxybutanedioate
A
ethyl 3-(t-butoxy)-2-(ethoxycarbonyl)propionate
B
diethyl (cyclohexylmethyl)propanedioate
C
ethyl diethyl malonate
D
Diethyl methylmalonate
Conditions | Yield |
---|---|
In cyclohexane Ambient temperature; Irradiation; photolysis of further t-butyl percarboxylates in various solvents; | A 40.8% B n/a C 1.3% D 37% E 1.7% |
diethyl ethylidenemalonate
t-butylmanganese chloride
A
diethyl 2-(3,3-dimethylbutan-2-yl)malonate
B
ethyl diethyl malonate
Conditions | Yield |
---|---|
In tetrahydrofuran at -30℃; for 2h; | A 10% B 40% |
diethyl ethylidenemalonate
A
diethyl 2-(3,3-dimethylbutan-2-yl)malonate
B
ethyl diethyl malonate
Conditions | Yield |
---|---|
With t-butylmanganese chloride In tetrahydrofuran at -30℃; for 2h; var. organomanganeses.; | A 10% B 40% |
2-Ethyl-2-(2-phenylsulfanyl-acetyl)-malonic acid diethyl ester
A
diethyl (acetyl)ethylmalonate
B
ethyl diethyl malonate
Conditions | Yield |
---|---|
With nickel In acetone | A 20% B 24% |
2-acetylpropanoic acid ethyl ester
ethyl 2-bromopropanedioic acid diethyl ester
ethyl diethyl malonate
2-Ethyl-3-oxo-succinic acid diethyl ester
ethyl diethyl malonate
Conditions | Yield |
---|---|
at 160℃; |
ethanol
propane-1,1,1-tricarboxylic acid triethyl ester
sodium ethanolate
A
ethyl diethyl malonate
B
Diethyl carbonate
ethanol
1,3-diethyl-2,4-dioxo-cyclobutane-1,3-dicarboxylic acid diethyl ester
sodium ethanolate
A
monoethyl DL-ethyl-malonate
B
ethyl diethyl malonate
2-ethyl-3-oxo-acrylic acid ethyl ester
sodium methylate
ethyl diethyl malonate
Conditions | Yield |
---|---|
With diethyl ether; nickel under 73550.8 - 95616 Torr; | |
With ethanol; nickel under 73550.8 - 95616 Torr; | |
With palladium Hydrogenation; |
Conditions | Yield |
---|---|
at 250℃; |
ethyl bromide
sodium ethanolate
ethyl acetoacetate
diethyl malonate
A
ethyl diethyl malonate
B
ethyl 2-ethyl-3-oxobutanoate
sodium diethylmalonate
ethyl iodide
ethyl diethyl malonate
Conditions | Yield |
---|---|
With diethyl ether | |
With ethanol |
ethyl diethyl malonate
monoethyl DL-ethyl-malonate
Conditions | Yield |
---|---|
Stage #1: ethyl diethyl malonate With potassium hydroxide; water In ethanol Stage #2: With hydrogenchloride In water pH=2; | 100% |
With hydrogenchloride; potassium hydroxide 1.) EtOH, room temp.; overnight; | 95% |
With potassium hydroxide In ethanol for 24h; Ambient temperature; | 73% |
linolenyl tosylate
ethyl diethyl malonate
ethyl (all-Z)-2-ethyl-2-ethoxycarbonyl-11,14,17-eicosatrienoate
Conditions | Yield |
---|---|
Stage #1: ethyl diethyl malonate With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide at 0 - 20℃; for 0.5h; Stage #2: linolenyl tosylate With sodium iodide In tetrahydrofuran; N,N-dimethyl-formamide at 70℃; for 2h; | 100% |
Conditions | Yield |
---|---|
With sodium methylate In methanol for 16h; Reflux; | 99% |
benzyl 2-fluoro-5-nitrobenzyl(methyl)carbamate
ethyl diethyl malonate
diethyl 2-(2-((((benzyloxy)carbonyl)(methyl)amino)methyl)-4-nitrophenyl)-2-ethylmalonate
Conditions | Yield |
---|---|
Stage #1: ethyl diethyl malonate With sodium hydride In dimethyl sulfoxide at 20℃; for 0.333333h; Stage #2: benzyl 2-fluoro-5-nitrobenzyl(methyl)carbamate In dimethyl sulfoxide at 65℃; | 98% |
ethyl diethyl malonate
4-Allyloxymethylbenzyl chloride
Diethyl 2-(4-allyloxymethylbenzyl)-2-ethylmalonate
Conditions | Yield |
---|---|
Stage #1: ethyl diethyl malonate With potassium tert-butylate In toluene for 0.5h; Heating; Stage #2: 4-Allyloxymethylbenzyl chloride In toluene for 6.5h; Heating; | 97.7% |
ethyl diethyl malonate
epichlorohydrin
2-carbethoxy-2-ethyl-4-(chloromethyl)butyrolactone
Conditions | Yield |
---|---|
With potassium tert-butylate for 12h; Heating; | 97% |
With ethanol; sodium ethanolate Behandeln des Reaktionsgemisches mit wss. Salzsaeure; |
ethyl diethyl malonate
2-nitro-N-(phenyl-λ3-iodaneylidene)benzenesulfonamide
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃; for 18h; | 97% |
2-Methylpyrimido<1,6-a>benzimidazole-1,3-(2H,5H)-dione
ethyl diethyl malonate
4-Hydroxy-2-methyl-5-ethyl-1H,6H-2,6a,10b-triazafluoranthene-1,3,6(2H)-trione
Conditions | Yield |
---|---|
With trichlorophenol at 280℃; for 0.5h; | 96% |
ethyl diethyl malonate
diethyl 2-chloro-2-ethylmalonate
Conditions | Yield |
---|---|
With potassium carbonate In tetrachloromethane | 96% |
acrylonitrile
ethyl diethyl malonate
diethyl 2-(2-cyanoethyl)-2-ethylmalonate
Conditions | Yield |
---|---|
With potassium tert-butylate In tert-butyl alcohol at 0 - 25℃; for 1h; | 95% |
With potassium carbonate In tetrahydrofuran; 1,2-dimethoxyethane at 65℃; for 8h; | 92% |
With 1,4-dioxane; N-benzyl-trimethylammonium hydroxide at 30 - 40℃; |
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran for 72h; Reflux; | 95% |
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 72h; Inert atmosphere; Reflux; | 95% |
With lithium aluminium tetrahydride for 14h; Reflux; Inert atmosphere; | 95% |
Conditions | Yield |
---|---|
With sodium hydroxide In water for 2h; Heating; | 95% |
With potassium hydroxide In water for 2h; Heating; | 94% |
With potassium hydroxide; water ueber mehrere Stufen; |
4-(bromomethyl)-4'-methyl-2,2'-bipyridine dihydrobromide
ethyl diethyl malonate
Conditions | Yield |
---|---|
Stage #1: ethyl diethyl malonate With sodium hydride In N,N-dimethyl-formamide for 0.5h; Metallation; Stage #2: 4-(bromomethyl)-4'-methyl-2,2'-bipyridine dihydrobromide In N,N-dimethyl-formamide for 5h; Alkylation; | 95% |
2-propynyl chloride
ethyl diethyl malonate
diethyl 2-ethyl-2-(1-propyn-3-yl)malonate
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 6h; | 95% |
[N-(p-tolylsulfonyl)imino]phenyliodinane
ethyl diethyl malonate
diethyl 2-(1-(4-methylphenylsulfonamido)ethyl)malonate
Conditions | Yield |
---|---|
With 1,10-Phenanthroline; 2,6-di-tert-butyl-4-methyl-phenol; copper(II) bis(trifluoromethanesulfonate) In dichloromethane at 20℃; for 18h; Molecular sieve; Inert atmosphere; | 95% |
[N-(p-tolylsulfonyl)imino]phenyliodinane
ethyl diethyl malonate
A
diethyl ethylidenemalonate
B
diethyl 2-(1-(4-methylphenylsulfonamido)ethyl)malonate
Conditions | Yield |
---|---|
With 1,10-Phenanthroline; copper(II) bis(trifluoromethanesulfonate) In dichloromethane at 20℃; for 4h; Molecular sieve; Inert atmosphere; | A 2% B 95% |
ethyl diethyl malonate
Conditions | Yield |
---|---|
Stage #1: ethyl diethyl malonate With potassium tert-butylate In dimethyl sulfoxide at 20℃; for 0.5h; Schlenk technique; Inert atmosphere; Stage #2: 6-(difluoro(phenylsulfonyl)methyl)phenanthridine In dimethyl sulfoxide at 20℃; for 24h; Schlenk technique; Inert atmosphere; | 95% |
4-hydroxy-1,6-dimethylpyridin-2(1H)-one
ethyl diethyl malonate
C12H13NO4
Conditions | Yield |
---|---|
In diphenylether Heating; | 94% |
Conditions | Yield |
---|---|
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 6h; | 94% |
With caesium carbonate In N,N-dimethyl-formamide at 20℃; | 89% |
2,6-Diaminopyridine
ethyl diethyl malonate
7-amino-3-ethyl-1,2-dihydro-4-hydroxy-2-oxo-1,8-naphthyridine
Conditions | Yield |
---|---|
In diphenylether for 0.5h; Heating; | 93% |
benzalacetophenone
ethyl diethyl malonate
ethyl-2-carbethoxy-3,6-diphenyl-2-ethyl-5-oxopentanoate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane under 7500600 Torr; for 70h; Ambient temperature; | 93% |
With potassium hydroxide; N-benzyl-N,N,N-triethylammonium chloride for 2h; Ambient temperature; | 75% |
With tetrabutyl ammonium fluoride In tetrahydrofuran at 30℃; under 10000 Torr; for 48h; | 35% |
2-bromonicotinonitrile
ethyl diethyl malonate
2-(ethyl malonic acid diethyl ester), 3-cyano pyridine
Conditions | Yield |
---|---|
With potassium tert-butylate; ammonium chloride In ammonia for 0.166667h; Irradiation; | 92% |
1-bromomethyl-2-[(phenylsulfonyl)methyl]benzene
ethyl diethyl malonate
4-Benzenesulfonyl-2-ethyl-3-oxo-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran Ambient temperature; | 92% |
Conditions | Yield |
---|---|
With sodium methylate In toluene for 5h; Heating; | 92% |
Conditions | Yield |
---|---|
In diphenylether at 200 - 220℃; | 92% |
1-bromo-6-benzyloxyhexane
ethyl diethyl malonate
diethyl 2-(6-(benzyloxy)hexyl)-2-ethylmalonate
Conditions | Yield |
---|---|
Stage #1: ethyl diethyl malonate With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 1.5h; Inert atmosphere; Stage #2: 1-bromo-6-benzyloxyhexane In N,N-dimethyl-formamide; mineral oil at 20℃; for 3.5h; Inert atmosphere; | 91% |
Stage #1: ethyl diethyl malonate With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 1.5h; Inert atmosphere; Stage #2: 1-bromo-6-benzyloxyhexane In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 3.5h; Inert atmosphere; | 91% |
5-oxabicyclo<2.2.0>hex-2-en-6-one
ethyl diethyl malonate
Conditions | Yield |
---|---|
Stage #1: ethyl diethyl malonate With sodium hydride In tetrahydrofuran at 20℃; Inert atmosphere; Stage #2: 5-oxabicyclo<2.2.0>hex-2-en-6-one With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; diethyl ether at 0℃; Inert atmosphere; Stage #3: With hydrogenchloride In water pH=Ca. 2; Inert atmosphere; diastereoselective reaction; | 90% |
Molecular Structure:
Molecular Formula: C9H16O4
Molecular Weight: 188.2209
IUPAC Name: Diethyl 2-ethylpropanedioate
Synonyms of Propanedioicacid, 2-ethyl-, 1,3-diethyl ester (CAS NO.133-13-1): AI3-19481 ; Diethyl 2-ethylmalonate ; Diethyl ethylmalonate ; EINECS 205-093-3 ; NSC 8706 ; Malonic acid, ethyl-, diethyl ester (8CI) ; Propanedioic acid, ethyl-, diethyl ester
CAS NO: 133-13-1
Classification Code: Pharmaceutical Intermediates ; TheMalonateRamificationProducts ; C8 to C9 ; Carbonyl Compounds ; Esters
Melting point: 0°C
Index of Refraction: 1.425
Molar Refractivity: 47.25 cm3
Molar Volume: 184.4 cm3
Surface Tension: 31.5 dyne/cm
Density: 1.02 g/cm3
Flash Point: 88.3 °C
Enthalpy of Vaporization: 44.8 kJ/mol
Boiling Point: 211.7 °C at 760 mmHg
Vapour Pressure: 0.18 mmHg at 25°C
Propanedioicacid, 2-ethyl-, 1,3-diethyl ester (CAS NO.133-13-1) is used as the medicine raw material and the agricultural chemicals intermediate.
Hazard Codes of Propanedioicacid, 2-ethyl-, 1,3-diethyl ester (CAS NO.133-13-1): Xi
Risk Statements: 36/37/38
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 24/25-36-26
S24/25: Avoid contact with skin and eyes.
S36: Wear suitable protective clothing.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
WGK Germany: 2
HS Code: 29171990
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